Ask the Readers: How Do You Build a Wardrobe on a Budget?

If you were building your wardrobe from scratch, how would you do it? Would you prioritize quality? Would you emphasize cost? Or is there some happy balance between the two? That’s what GRS reader author J.D. wants to know. He writes:

I’m a 40-something guy who’s lost 40-something pounds over the past year. This is a good thing. But now my old clothes don’t fit. As a frugal fellow, this creates something of a dilemma. How do I re-build my wardrobe while keeping an eye on costs?

For most of my adult life, I’ve dressed in what I’d call Modern Slob. Or maybe Geek Casual. My wardrobe comprised jeans, t-shirts, and sweatshirts, most of which were purchased at Costco and local thrift stores.

Now that I’m slimmer, I’m more interested in dressing well. That is, I want to look nice, and not like I don’t give a hoot. I don’t need to buy a suit, but I’d like to learn how to buy affordable clothing in classic fashions. I don’t know where to start.

First, I’ll stop referring to myself in third person. (It’s like a bad Seinfeld episode or something.) Next, I’ll elaborate on my concerns.

I really do have something of a wardrobe crisis. Downstairs in the living room, I have a pile of clothes that no longer fit. I’m gradually giving these away to friends and family (and will donate the rest to charity), but meanwhile there’s little left to wear. I don’t need to rebuild my wardrobe to the size it was before my wardrobe project, but I do want to have some essentials on hand. Right now, I have no dress shirts that fit. And no dress pants. And no turtlenecks. And no jeans.

I could go on a shopping spree at the local mall, I suppose, but that’s so not me (and on so many levels). I’ve tried to buy some new clothes at Costco, but I don’t like the fit and fashions they offer right now. That leaves me with the thrift stores, but these are an imperfect solution. I’m truly puzzled about how to build a wardrobe on a budget.

Affordable fashion?
Lately, out of curiosity, I’ve been reading magazines like GQ and Esquire. I haven’t done this in 20 years. (And once this spell passes, it’ll probably be another 20 years before I pick them up again.) While entertaining, there are a couple of problems with modern fashion mags:

I have zero interest in buying “fashionable” clothing. I abhor the idea of owning something that’s hip today but which may be unwearable five years from now. I’m drawn to what Alan Flusser calls “permanent fashion“. (And the casual end of that.)

I’m not willing to pay big bucks for clothes. I cringe when I read things like: “Yes, you could buy a cashmere sweater for $90, but why would you? Top quality costs ten times as much, but it’s worth it.” Not to me, it isn’t. No sweater is worth $900. Remember, I’m accustomed to buying sweaters for $9 at Goodwill.

Surely there’s a balance to be had. There must be fine clothes available at reasonable prices, especially for folks like me who don’t give a whit about labels. I just want quality. (And although it pains my frugal nature, I’m willing to admit that maybe paying a little more for quality is worth it.)

Does quality trump cost?
For example, I recently bought an Icebreaker merino wool t-shirt on sale at REI for $45. I felt guilty about this for days (because it’s three times what I’d usually spend on a t-shirt), but then I wore it during our trip to Europe. I loved it. The shirt felt great, but best of all, it never stank — even after I wore it for a week straight. (No joke.) If that t-shirt holds up to wear, it’ll be worth $45 in my book, and I’ll no longer feel guilty about buying it.

But I’m not willing to spend $45 each on a drawer full of t-shirts. That’s crazy, right? Plus, I’m not ready to rule out thrift stores. I can buy great stuff there for cheap. Just last week, for example, I went thrift-store shopping with Kris and her sister. I was giddy to find one of my favorite shirts — one that I’ve purged because it’s too large — in size medium. For five bucks. (Then I found two more from the same company that I picked up, too.) And just yesterday, I bought a nice-looking pair of name-brand corduroy pants for $6 at another thrift store.

If thrift stores are so great, why don’t I use them exclusively? Well, they’re a great way to supplement the clothes you already have, but it’s tough to use them to build a wardrobe from scratch. Their selection is…random. And there’s no co-ordination between styles.

Help me help myself
So, dear readers, I need your help. Tell me: How do you find affordable clothing? If you were building a wardrobe from scratch, where would you start? Is it feasible to do this just using thrift stores? Are you willing to pay more for quality? How much more?

Finally, can you recommend any websites about dressing well? (I’m especially interesting in learning how to dress well on a budget.) Or maybe I should forget about looking nice and just go back to being a modern slob!

One of the things I find most important with men’s clothing is: Does it fit properly? I would find your optimum pants and buy in three colors, maybe black, olive green, and tan or whatever colors you feel most comfortable in. Then find button down shirts to go with them. Ideally each shirt should go with at least two pair of the pants. Last time I did this we were able to get the basic pieces for under $200. Finding stores sales can help. Add at least one jacket that fits your lifestyle, leather comes to mind as it can be both casual or dressy. People don’t expect men to cater to the newest style so much as is it clean and pressed so get easy care fabrics that don’t wrinkle. I think it’s much easier to buy all the basic pieces at once than to approach things like a scavenger hunt where things never seem to look right together. I recently did a post on the subject for women that your readers may enjoy. http://inthetrenches2009.blogspot.com/2010/10/back-to-work-wardrobe-on-budget.html The photos aren’t great but you get the idea. Have fun! A whole new you!

Some great advice here, I’m always amazed at my friend who is in the costuming business in the movies…she dresses well all the time and I know she does not spend much. She follows some of the advice here and goes to expensive stores off season and gets stuff on sale.
Something I do, partly because I don’t have the kind of mind that just knows what to wear for some reason, I look up pictures of people that I have admired and see what they wear. It never fails to give me ideas. I just recently looked up Ali McGraw, I love her style and heard her say on tv that she only wears a few pieces of clothing …. she has a style that I admire so it helps to look at pictures to see what she is wearing to see if I might get ideas.

I am extremely brand conscious…at the Goodwill. I’ve found I love Express jeans in one particular size, so I buy them every time I see them. If I don’t need them now, they go in a drawer so when my current ones wear through, poof!, new clothes! I won’t buy Walmart brands (george, new boundaries, faded glory) because they fray in two washings. I’ll buy all the basics in Polo and Klein I see (they last forever) and I have a soft spot for cashmere…I’m up to five cashmere sweaters. But shopping like this takes time. You can’t go in with a goal (i.e., good quality brown shoes). You have to take it as it comes.

First of all, good for you JD! This is what I call a good problem to have. Hilarious to phrase this as a reader question by the way.

Here is my take – focus on QUALITY over QUANTITY. Since you want to live a simplified life and you aren’t into clothes and fashion, this makes perfect sense for you. Here are the steps:

1) Create a list of what you want your basic wardrobe to consist of. Here is an example
– 2 nice pairs of jeans
– 2 nice pairs of slacks – one black one brown or grey
– 3 button down dress shirts
– 2 nice sweaters that can be worn on their own or over button down shirts
– 1 black jacket with hood that can be worn casual but is nice enough to wear with dress slacks (I’m also from a rainy west coast climate and I think this is essential!)
– 5 great quality t-shirts.

Again, this is just an example.

2) Next step is to look in your closet. Are you already fulfilling any of these requirements with clothes that you already own? If so, check them off your list.

3) What you have left is your shopping list. You don’t need to buy everything in one day, but now you have a list to keep with you in your wallet and know what you’re looking for when you go to a store. This will make the shopping experience less overwhelming. When you walk into a store you know exactly what you are looking for and you can cross it off the list when you buy it.

4) Decide on standards. For example, I am adamant that I do not buy clothes that wrinkle easily. (I test the clothes by scrunching up a handful of the fabric and holding it for a second or two. If it comes away a wrinkled mess it doesn’t make it to the fitting room). Maybe you’ll decide you want items only in a certain fabric, colour that you know you’ll love, or whatever. Stick to your standards.

5) Shop. In my opinion, you can’t get your wardrobe staples at Thrift Stores. Sorry. I love thrifts stores too but just being in them makes you relax your standards. If you really want to go used at least try consignment shops. And ok, maybe for jeans. Because who doesn’t like buying pre-broken in jeans? Especially jeans that cost $200 new and $40 at the consignment shop.

And forget online shopping. Sorry. You HAVE to try on their pieces and people are normally a little more apathetic about fit when online shopping since the returns are a hassle. FIT IS PARAMOUNT.

What I would do is try several different stores. In the end you’ll find a few where the items just seem to fit your body (such as REI which you’ve already identified). You don’t have to try stores all in one day, you can try them gradually as the mood moves you. And you don’t have to buy on the day that you find a store that makes jeans (for example) you like. Take your time. You can even go home and sign up for the store’s email list so that you’ll know when their next big sale is and you can do your shopping then. Main stream stores have so many big sales that it’s a real shame to buy full price.

6) Shop at stores with good return policies. That way you can bring the item home and take a second look before committing. It’s also nice to get a 2nd opinion (like from Chris or someone else who has nice taste and will tell the truth) when you’re spending a little extra.

Good luck JD! As you’ve already discovered, it’s far better to own a few pieces that you love to wear and look great in rather than a big pile of junk.

I have great luck with consignment stores (Mpls area) and a few of them have an impressive selection of quality men’s clothes at great prices. I’d check to see if there are any in your area that carry men’s. Especially if you aren’t in a hurry, you can take the time to browse and see if there are a few things with your name on them…

Hey J.D, I’m not sure if this was already mentioned as I didn’t have time to read through all of the comments, but…

When I became a teacher a few years ago and needed a more professional wardrobe for very little $$, I started trading in clothes that I already had, but never wore to a quality consignment shop in my area. You could either wait for your items to sell and get cash, or get store credit. Although it wasn’t as cheap as the Salvation Army, I still got plenty of things for low costs – dress pants for $12 or $14, sweaters for $15… I can’t imagine shopping at a mall anymore, as all of these items were in terrific shape, and some still had the tag on them.

For folks with kids, I do this same thing with our local consignment shops – as my youngest grows out of a stage of clothes, I bring them in for credit, and get newer “big clothes” for my oldest boy, which will later become hand me downs for my youngest.

Hi,
Not sure if someone else hasn’t suggested this, but if you find a brand you like and know the clothes in a size fit the way you like, go to Ebay and see if you can buy the items that you seek. As an example, you can put in black turtle neck, Ralph Lauren (designer or brand that you know you like ), NWT (new with tags) and see what comes up. I’ve had great luck buying particular items this way. You can select “buy now” as an option so you don’t have to wait around for an auction to finish. You can find items with free shipping. It really is cost-effective and fun when you know what you want to buy.

I’m a frequent Ross and TJ Max shopper. These places really offer great buys on clothes. You have to hunt, and sometimes there is utter crap, but I typically find dockers pants, cashmere sweaters, stuff from LL Bean and Columbia (outdoor clothing company) at great prices.

I suggest choosing 2-3 stores that make great clothing that’s stylish yet classic, and then you can focus on their clothing and on learning how their sales work.

Two easy ones to start with are Banana Republic and The Gap. Check them out, especially Banana. It fits your style, and the men’s clothing is quality, stylish and classic. It’s also of reasonable quality. And the sales are AWESOME. First, check the sale section whenever you happen to be by one and at the end of each season. Be sure to go shopping after Christmas and in January. Last year I got a dozen sweaters and pants for $9.99 to $19.99 (sometimes $29.99) that were all originally $59-120. Second, use a junk email address and be sure that you are on all of their mailing lists. Almost all companies have great sales for “insiders.” Banana Republic regularly sends me coupons for 25-40% off of everything on certain days.

Another benefit to choosing to rely on a store like Banana Republic is that you can somewhat go on auto-pilot and trust their style to make up for any fashion judgment that you lack. If someone lacks fashion sense and then that person shops at places like Costco or vast department stores, there are way too many ways that you can go wrong and too many ways to end up looking like a frumpy fashion disaster.

J Crew is another place to try, but a little more expensive than Banana and The Gap.

As I read through more of these suggestions, I must say please at least check out stores like J Crew, Brooks Brothers and Banana Republic! Some people are suggesting stores that make a few great items and lots of cheap-looking items or stores that have some good fashion and piles and piles of ugly clothing that will never help you look like anything but frumpy or outdoorsy (JC Penny, some of the outdoors place, etc). Smaller stores like the ones listed in the first sentence have a pre-selected group of clothing so you don’t have to search or stress too much, and the sales are amazing.

I buy pretty much all my husband’s clothes (very housewifey of me, I know, but aside from his outdoor gear he’d wear things until they totally disintegrated before he’d think to replace them and since I care….) One place that I didn’t see anyone mention where I find great deals for more casual basics (especially pants–Dockers, Levis, Columbia, Carhartts) is Fred Meyer. They’re often on sale (I don’t buy unless they are) they’re open early/late, I have to go there for other stuff anyway, and there’s no pressure at all to buy something if there’s nothing you like.

I rarely have the patience for Ross/TJ Maxx and while I’ll buy polos/tees/boxers at places like Old Navy or Target I think their pants and dress shirts are usually pretty chintzy looking. I always feel like I’m getting scammed at outlets. I do, as many others noted above, often find great deals on dressier pants/shirts/sweaters on the clearance racks at Banana Republic.

Icebreakers definitely rock. Nthing Sierra Trading Post for deals there. You can also brave an REI garage sale if you’re up for that sort of thing.

I usually start with H&M for good, attractive and washable basics like sweaters and dress shirts and then slowly replace those items with higher quality discounted finds at more expensive stores like Loehmann’s, Off 5th, and Nordstrom Rack to give my wardrobe dimension. No one can tell the difference between an H&M shirt and a higher quality brand when I wear them, and are often surprised and admiring of my frugal fashion savvy when I disclose that I made the purchase from H&M (or also when I disclose that I purchased them from a thrift store on Haight Street here in San Francisco). J. Crew is a great store for affordable classics and has great sales a few times a year and a good markdown area all year round.

Depends on what you mean by “affordable”. However I can offer this. As a woman with a senior job that requires looking decently put together, I finally hired a wardrobe consultant, because though I like nice clothes I do not like shopping. I found her online.

My consultant shops with me (she charges $50/hour but is unbelievably efficient), has cleared the junk out of my wardrobe, does needed alterations, and sews from scratch to a couture standard. She is worth every penny I pay. In addition, I have learned from her how to shop more efficiently. An example- I have never owned a pair of blue jeans I actually liked-I loathe jeans shopping. We went out about 3 weeks ago to buy jeans. She made me try on at least 35 pairs (I wd never have had the patience if I had gone alone), and I returned with 4 pairs of perfectly fitting jeans in different styles (straight/boot cut/skinny) and an understanding of what brand fits my shape (Tommy Hilfiger). 2 pairs didnt need hemming, 2 did. She did the hemming in time for a trip deadline. She brings any coupons and knows where the sales are, what inventory stores carry, and the best times/days/seasons to shop. When I add it up, with discounts, I am probably paying as much as I would have done if I shopped alone, but I like my clothes MUCH more, THEY FIT, and my wardrobe works together better as a whole. She works around my budget. I can now buy stuff myself to fill the gaps, though I usually ask her what she thinks afterwards.

My particular challenge is that I need accessories (shoes, bags, jewellery) that work with both Western and Indian clothes-she has been very helpful in this regard and I might take her sari shopping some time.

Stylists for men exist, if you want to go that route.

I NEVER EVER shop at thrift stores-too slow and time consuming not to speak of the junk you need to weed through-it is simply not efficient if you are time stressed, and there is a reason the stuff is cheap.

My consultant told me I lack accessories, so I now shop for classic basics and buy more accessories-it really makes dressing much more fun than it was! I prefer to buy fewer better quality items, so I dont mind paying full price. Even with alterations, they are a better investment.

You may want try to buy clothes at a second-hand / consignment-type store versus your typical Goodwill / Salvation Army type deal. I personally love shopping at Plato’s closet in Virginia. It’s like a thrift store, except for people bring in their clothes to sell, and the store only chooses more fashionable or certain name brand clothing to buy. So you are more likely to get a hit than a miss; although, it tends to be a little costlier than a thrift store, but a good 75% off if you had bought it brand new. So trendy but cheap.

I’ve not read all the responses as I have been ill and behind on the reading. That said, I’ve lost fifty pounds and am still losing. Therefore, I only buy two or three bottoms at a time untill I reach my goal..and a few more on top. I accept that I will have fewer choices until I reach my goal weight and happen to think thats a fair trade…

I’ve read your blog for about a year now and most of my friends would laugh to know that the first time I’m leaving a comment has to do with shopping for clothes. Clothing on a budget is my forte. Expensive taste on a budget is my life mission. Fashion is always important to me.

So I am one of those people who WILL pay for a $90 sweater…quality is really that important to me. Let me explain. I love Target. And, I love J Crew. Places like J Crew that make quality clothing will last you so much longer than other stores like Target, and even GAP, Banana Republic (depending on the item) and Old Navy. With that said, I’ll buy supplementary clothing from those places, meaning: If I’m unsure if it will be in style next year, I won’t buy the expensive version. Or if it is something like a scarf or socks or a tshirt, I will buy it. But I pay for quality for staple items. Why? Because it lasts. I have clothing from J Crew that has stayed with me from college (I graduated in 2002). I do not own a thing from 2002 that is from any other store other than a wool coat from GAP that the lining is just now ripping out of the insides. Technically it’s from 2003 but I’m surprised the coat has lasted this long. A pair of dress pants from JCrew cost $150 but they lasted me for 4.5 years. No pant from a cheaper store will last me that long. And, yes. I promise I don’t work for JCrew.

Here are my bullet point thoughts on how I purchase nice clothing items.

-I rarely pay for it full price but if it’s a good item, it’s worth it. Always.

-Buy your basics in quality. It just makes sense. Jeans, coats, shoes…not only do you look nicer but it’s fiscally responsible. For me, there are some things that just don’t last from season to season no matter what the quality. So I’ve learned over the years that white tshirts, most winter sweaters and pretty much any knit clothing will need to be replaced after 1-2 seasons for me just because they break down, stain or shrink faster with me. Don’t know why but they do. So I don’t pay a lot for those unless it’s really on sale. You’ll have things like that where you’ll learn they aren’t investment pieces for you like they are for others so you’ll think twice before you buy. That only comes with time.

-Since I’m love fashion, I will notice quality pretty quickly on others and have an appreciation for well tailored clothing. Quality fits better. One trick I have for myself is that I will buy one really “expensive/quality” item and then offset it with a not so expensive item. For instance I will buy a pair of designer jeans on sale that last for a couple of years…then I will buy a tshirt from Target. Adding quality with lesser quality still makes your outfit look good. (Not sure if you’re concerned with that but it’s my trick to always looking great).

-I’m sure you know this but ALWAYS ask about a sale. Sales people will sometimes divulge an upcoming sale, especially if you shop there often. Ask. Ask. Ask. Student discount, loyalty club discount (not credit cards), military discount, first time buyer discount. “Are you having a sale in the next couple of weeks?” I ask it often. Once I had a store hold a dress for a week for me because they were having a sale for 20% off that weekend. A lot of places have sales going on and don’t tell you till you get to the register.

-Some stores will waive shipping if you place the phone order in the store (JCrew does this as a standard practice). If not ask. Always ask.

-Buying quality can pay off if it shrinks, tears or just plain doesn’t work out. Norstrom, JCrew, Anthropologie, REI (just to name a few) will take back an item without a receipt at ANY TIME if you are unsatisfied. I wore a pair of KEEN shoes in Hawaii in July that I bought from Nordstrom just for that trip and hated them because my heel kept pushing back to the rim of the sandal, thus making my hiking miserable. Normally I love the brand so I was surprised it happened. Nordstrom took them back (dirt and all) just because I said they did not fit well. JCrew took back a button down after it shrank in the wash and Anthropologie took back a really expensive pair of jeans after they tore 6 months later. Just keep your receipts.

-This is pretty well known across the board but buy clothing items after they go on sale at the end of the season. I’m actually finding that because most stores put fall clothing out in August/July, it starts going on sale by October/November (sometimes even in September) and certainly by the week or two after Christmas it’s discounted significantly. It’s still cold outside during those times so technically I’m not having to buy a coat when it’s still warm outside and then wait all year to wear it. Start looking for sale items mid-season.

-Other tricks I use are to bookmark items that I really like and want to buy and then go back to them online to see when they go on sale. Also, if you order online always google “(name of store) online coupons” and see what happens. I almost always save on something.

-Finally, because fashion is so important to me for many reasons, I post a lot of inspiration pictures of outfits that I really like torn out of catalogues on my walls. Having the reminders up lets me keep an eye out for the clothes when they on sale but it also help me keep the “eye on the prize” so I don’ waste my money on frivolous purchases I won’t want later. (That’s also a financial trick I do for myself as well. Fashion is that important to me so I’ll strive to make a way to buy something that’s out of my budget when it goes on sale, or just save for it or make it work somehow. Keeping pages up on my walls near my dresser also gives me inspiration to make my closet work for me…often I can get a look with what I already have.)

One man’s comic book collection is another woman’s designer jeans collection.

I really like what Micah Smith said about clothing being an investment portfolio. So true. Balance it out across the board but put your money wear it counts. If a $45 shirt from REI lasted you for that long, axe the guilt and appreciate a well made purchase.

I started my first ever permanent business casual dress code job Monday before thanks giving.

I am a 26 year old tom boy, my closet is dominated by jeans and t-shirts. Very little in the way of business casual clothing. I have been on unemployment most this past year so I didn’t have a lot to flesh out a weekly work wardrobe.

I went Black Friday shopping. Picked up a good comfortable pair of shoes usually $110 for $70 also I picked up some nice sweaters for almost 50% off usual price.

Also I subscribe to the Consumerist blog. Every morning they have a “morning deals” post. The week the job was offered to me there was a 30% off entire purchase at Old Navy coupon mentioned in the morning deals post. I used this to get some khakis.

Hey J.D. — Did you know that REI has a used gear sale every couple of months? This is right up your alley — tons of great gear and clothes on major sale. Most of the items are gently used and are returned for various reasons like “I didn’t like the color” or “This jacket was too long”. These reasons are far better than “Moths ate the sleeves”! I would check with your local REI store to find out details. They aren’t announced very far in advanced so you have to call and ask when the next one is if you don’t shop at the store often enough to find out when you are there. At our best used gear sale shopping experience, my husband and I walked away with a rain/wind jacket, a fleece, and 6 pairs of climbing shoes for less than $100! Just one pair of climbing shoes costs over $100 – everything was like new! Great deals!

I will have to say that I think stores like TJ Maxx, Marshall’s, Loehmann’s, Nordstrom Rack, etc. are all excellent. Right now, Loehmann’s is my absolute favorite right now. If you sign up for their Rewards card, you will ALWAYS be receiving coupons in the mail, or email. These are usually 20, 30% off entire purchases including sale and clearance prices. These stores benefit from frequent visits. Befriend an associate or chat one up and find out when their store usually puts out new merchandise. You will find excellent quality and very good prices.

They wear the exact same thing every time. Personally, I find it boring. I think you’re better off developing your personal sense of style and then building on that. For inspiration on breaking out of your comfort zone, check out the Sartorialist. http://thesartorialist.blogspot.com/

P.S. One thing I will NOT advocate is spending a lot of money on jeans. That whole expensive jeans thing is bull and a complete product of our 2000′s overspending boom. The best jeans are 100% cotton. Find a brand that fits you nice and stick to it. Simplify. I’ve tried on several pairs of jeans including these ridiculous “designer” jeans. They do NOTHING for me. My best-fitting jeans are the pair I got on sale at Gap and Express for $19 – $35 about six years ago. They’re soft and fit gorgeously. I really think paying $100 for jeans is about as stupid as paying $45 for a cotton t-shirt. You’re paying for nothing but the label at that point, sorry. Unless it’s organic or egyptian cotton, those jeans and t-shirts are made out of the same type of cotton. And funny enough most of those designer jeans are made in china and other such countries. It’s amazing how easily and quickly we fall into these marketing traps.

Most of my clothes come from Gap or Banana Republic Outlets. I usually get button down shirts, jeans and khakis for $20-25, polos and t-shirts for $10-15 and they last at least 5-7 years. That’s good enough for me both in price and wear life. Lately I’ve been wearing the pants 2 or 3 times before washing to see if that extends the life.

If anyone knows a good place to buy plain white under-shirts that don’t stretch out in the neck or shrink, let me know. I’ve given up on Hanes & FOTL.

1) I would start rebuilding by focusing on a color palette. It is winter, so think all grays, browns/tans and pumpkin or squash for a pop of color. Why color? Because it keeps you focused at any store, be it thrift or Target. You get more outfits for less money as things mix-and-match better. And find the RIGHT shades — some colors (like what they offer at Old Navy) are “off” or obnoxiously too bright.

2) Each season, you rotate out clothes for new colors/clothes. That means you put them in bags and hide them. And then when you crack them out again next season, it’s like having bought a whole new wardrobe.

3) Lay down the money for better shoes, belts, shades and jeans, as people tend to notice these items first. If you don’t like designer jeans, get some classic Levis. The best of both worlds (comfort and never-ending style).

4) And the rule of scarves works for men, too, JD. A manly winter one will re-freshen up an outfit.

5) Always pay the money for something you always wear, like those REI shirts. Having 3 of those is better than having 9 of something else that equals the same amount of money, sans the dressing confusion. If you like what you wear, you’ll save time in the morning!

Clothing has always been one of the last things I spend money on, unless it’s a much-needed underwear and sock replenishment. I get money every year from my grandparents for my birthday and Christmas, and I’ve too often relied on that for wardrobe additions.

That being said, I have built a decent collection of work-appropriate shirts and pants by finding the brand/label that fits me well, and then hitting up their sales. Sure, I probably wouldn’t have bought that pink floral button-down tunic blouse if I’d seen it on the rack in a store, but when it was on sale for $20 from my favorite catalog vendor, I bought it and have worn it several times a month for the past four years. For me, work clothes serve a purpose and don’t have to reflect my personality or fashion preferences. If you can buy quality goods on sale and don’t mind that you’re getting the least popular options, then you’ll get a lot of wear for a little cash.

You need to think in terms of your personal uniform and clothing that is comfortable to you. You can buy those items at a store or on-line (best for utilizing codes and discounts prevalent during this time of year). I spend more money on my uniform pieces and consider them the staple of my wardrobe for years to come. Your uniform should be interchangeable pieces that can be worn with multiple items. If you buy a sweater that can only be worn with one pair of pants, it is more of a quirky item and not a uniform piece. Use thrift stores to find quirky one of a kind items. Think of these as your “fun” pieces or the “pop” in your everyday uniform. Also if you find a $6 pair of nice pants or a $17 jacket don’t underestimate tayloring. Often your local dry cleaner can provide you with simple alterations that will fit clothing to your body and make your bargain item fit to your body type. Best of luck to you!

I would recommend Sierra Trading Post http://www.sierratradingpost.com. They sell overstocks, seconds, etc. Their prices are always discounted. If you sign up for their newsletter, then they send out coupons for 20-40% off.

I’ve had two kids in 3 years, which means I’ve had about 4 wardrobes because my body changed differently each time. I’m also over 40, so who knows what is due to babies and what is due to being over 40. Anyway, my advice is to go to a large thrift store in an affluent area.

I would suggest devoting some time to it and trying on a LOT of different things. This is what I have done to rebuild my wardrobe at least 3 times in the past 5 years (once due to promotion, once while losing weight due to kid #1 and once while losing weight with kid #2).

The thing I like about thrift stores is that sometimes I end up trying on things that I wouldn’t in a regular store and really liking them.

I find high end items in my thrift store. I believe that is because it is in a wealthy area. The other thing I love about my thrift store is that they have shopping carts!

Considering you live in Oregon (I assume rainy and cold winter), age (late30s, early 40s?) and that you want to start from scratch I recommend you the following:

1st know what kind of colours suit you, for example I look great in red and royal blue, good in navy, black or white and bad in grey, sand or brown. Get to know which colours you like better, which might not be the ones you like more or the ones you’re used to.

2nd Get to know what kind of clothes/style fit better to you (and as you’re looking in the long run will keep fitting to you in ten years)

3rd Get basic clothes mixing what you like and a classic stile that will not be old fashioned in ten years using the colours and style you’ve decided before. I recommed you the following, it’s a bit preppy and classic but you can make an idea and change what you like:

-2 classic jeans (Levis 501 like), one dark blue and another light blue.
-2 chinos that go well with the colours that better suit you
-3 knit sweaters in different colours that fit you, I prefer cotton because is not itchy and you can wash them in washing machines, but it’s up to you.
-3 oxford cloth shirts in different colours that fit you, plus your white dressing shirt.
- 2 classic polos (colours that fit you, one dark and another one light)
- 2 coats one classic (Burberry like) and another for (Columbia, The North Face like).
- Stuff you like or to compensate your needs and style, for example if you find it too classic buy t-shirts and a hoodie) and needs (if you do outdoor activities like canoeing or cycling buy the appropiate stuff, you might need a suit for some occassions, maybe a blazer, etc).

I don’t say those brands, I just say the style like.

With that you have for multiple uses (going out for dinner, give talks, garage sales, etc). Combine them never using the same colour in the shirt and the jumper.

About buying them I’ll buy at sales/outlets etc good quality/good brands the ones you can find. The rest buy them cheap. After that with time drop your cheaper clothes as they get old with ones you buy in sales/outlets of better quality. Give yourself a budget and use it.

Dressing well takes more time than money, when you know what fits you well you’ll need less time. Ask your wife, if your female/gay/fashionist friends give you unsolicited compliments you’re on the right track.

And a last thing, it doesn’t matter how little you paid for something, if it doesn’t fits you or you don’t look good with it. If yo’re using it more than staying at home or working in the garden you’ve wasted your money.

Consider the “price per wear” – that awesome shirt at REI that cost a chunk of change was well worth its weight and money in travel. You’ll be using it until it gives out. So, when you buy nice shirts that might cost more, buy them in colors that coordinate or in things that won’t wear out as much. Even as a girl, I find myself buying the expensive, classic pieces in dark colors – it’s easy to ruin a white button down, harder to ruin a medium-blue button down.

The best resource you could want is a blog call “An Affordable Wardrobe”. Its done by a guy who gives great conventional wardrobe and men’s style advice and who’s motto is “Penury is no excuse”. He talks about dressing well for cheap by leveraging thrift stores.

JD -
I think you will like Well Suited. It is great for work clothes. I would echo some other people’s advice as well, get basic colors for work that go with everything. It makes the decision in the morning of what to wear easy. However, if you are not going into an office, a good pair of jeans and a Icebreaker T-shirt go along way.

I would love to get coffee if Well Suited works out. I am pretty sure you have email through the comments section. Good luck replacing the wardrobe.

please don’t buy cheap cashmere! see article. the only cashmere i would buy is at the thrift store (it may be worth darning a moth hole or two – get an expert knitter to help you or take it to a really good tailor).

JD – regarding dress clothes… First, I’m pretty cheap and hate (hate, hate, hate) to shop for clothes. However, I learned early in my career to buy classic dress shirts and pants. I pick several shirt/pant combo’s that can easily be mixed and matched so that with 3-4 shirts and a couple of pants I can easily switch it up. I add two nice blazers and I’m good for anything.

Next, buy QUALITY!! I always went to Joseph A Banks. I have bought top of the line dress shirts and pants from them that have easily lasted 7-10 years. Take good care of them on both the wearing/cleaning ends and you will have very long lasting clothes.

I recently needed a dress shirt and pants at the last minute on our trip around the world. I bought cheap and couldn’t believe how quickly they fell apart – never again!

I think a big key is finding 1-2 retailers you really like and shop exclusively (or as much as possible) with them. Find fits you like like a particular style of jeans or a button-down style so you can easily purchase different colors moving forward without too much work or having to go to the store.
Along with shopping exclusively, you can be part of their rewards programs. I know you may not be a proponent of a store credit card, but there are a myriad of benefits to having a GapCard, and if you pay it off each month, I don’t think its a big deal. You can use it cross-brand (Old Navy, Gap, & Banana Republic + outlets), and you get a ton of discounts and rewards. They offer up to 40% off deals via email, extra % on clearance, etc. I almost never buy full-price as they mark down pretty frequently. I do also shop with J Crew, which doesn’t seem really inexpensive, but the styles are really high quality & fit well. They are pieces I’ll have in my closet forever. I justify spending money on clothes that fit well b/c I’m really petite. I can echo liking Land’s End for quality pieces, and also really like their new Canvas line, which is a little hipper than the original as far as fit/style.
Also, I’d recommend buying as much as possible in neutral colors, like black, grey, navy, brown, camel, etc.

I would start with buying multi-purpose items. Solid color sweaters can be worn with jeans, dress slacks, under a sports coat, etc. They are very versatile. The same with basic button down shirts. Buy pieces that can be mixed and matched versus specialty pieces. A nice wool car coat is also a very versatile item.

Everybody has sales. I get short sleeve polos at Kohls, they last a couple of years but are only about $10. Certain things like that I’ll buy cheap, but not everything. Brooks Brothers has regular sales as well as corporate discounts.

One place I don’t skimp is shoes. A quality brand like Allen Edmonds will last years and can be recrafted and/or resoled.

I find that Express is very good, especially for basics, both casual and for businesswear. Some things are rip offs (like $20 tank tops) but they very often have great buy one get one sales, which can be combined with coupons. Their clothing generally comes in similar color schemes so it’s easy to mix and match all of their styles and colors. You have to be careful of what you’re buying, but as long as you’re constantly thinking of whether it’s worth buying an item, it comes out on top time and time again when I need to rebuild my wardrobe.

I confess I’ve only read through the first page (out of five!) of comments on this post, so if I’m repeating anyone…sorry.

It takes patience, but try Sierra Trading Post. In particular, check out the “classics” grouping. Not everything is super cheap, but most things are high quality, and some things definitely are super cheap. They carry many designer labels in last year’s or last season’s colors or styles. I generally avoid seconds and get overstocks, and even so find some ridiculous bargains.

They’re generally very good about returns (as long as you don’t buy a ton of stuff and return the vast majority of it…keep you return rate below 50% and they won’t hassle you about it). I’ve never had any kind of customer service issue from them. They are, apparently, run by evangelical Christians, but they don’t try to convert you or anything; I occasionally am a little surprised to see bible verses on the site but it’s never appeared to be over the top or proselytizing (and some people no doubt actively prefer to shop at an organization that is owned by Christians).

You can almost always find free shipping and other percentage-off coupons by using Retail Me Not or similar sites.

Once you’ve made your list of needs, organize in order of priority and just check the site occasionally. You’ll have to search through a lot – their inventory is staggering – but it pays off. You can use search terms (like “wool” or “cashmere” or “Schoeller”…some of my favorites) to narrow down the field a little. They often carry specific brands a lot, so if you find a brand you like you can usually get your size dialed in pretty well. And shoppers there are active commenters, particularly about fit.

Good luck, J.D.! And congratulations on your amazing weight loss…I read GFS, too, and have watched your progress with just a little bit of envy.

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